Time After Time - Cassandra Wilson

I’m a child of the eighties, so I love Cyndi Lauper and her original recording of this tune. But Cassandra Wilson found a whole new layer of meaning with her gentle jazz version. She slows the tempo way down, lowers the key to match her smoky contralto, and builds up layers of dreamy acoustic guitar and e-bow. The track is from an album she did called Traveling Miles, songs written or made famous by Miles Davis. This brings us to the troublesome issue of Miles’ music of the 1980s. If you’re not a jazz nerd, you may need a little context here.

It’s silly to try to define a best jazz musician ever, but if you had to pick someone, you could make a very strong case for Miles. He came up alongside the first generation of bebop players, replacing Dizzy Gillespie in Charlie Parker’s band in the 1940s. He spent the 1950s making one devastatingly great bebop album after another, at the center of a band that included such heavyweights as John Coltrane and Cannonball Adderley. At the end of that decade, he made Kind Of Blue, which, if you don’t have it, you should get it, you won’t be sorry. Then Miles spent the 1960s grooming a bunch of teenagers (including Herbie Hancock and Wayne Shorter) into another staggeringly great band. Miles’ music of that decade set the standard for intellectual adventurism that every college jazz program is still trying to match. And then Miles threw the entire concept of “jazz” out the window in the 1970s, turning instead to a kind of freeform acid funk inspired by Jimi Hendrix, with yet another bunch of teenagers who all went on to become jazz legends in their own right. This is an overwhelming swath of America’s musical culture to try and wrap your head around. My friend Leo, the best jazz drummer I know, commented once that while he wants to support his fellow contemporary jazz musicians by buying their albums, he could always just go buy yet another Miles Davis album instead and know that it’s going to be great.

In 1975, Miles stopped playing for five years due to health problems. When he returned, he wasn’t quite the same. He made albums all through the 80s, and some of them are okay, but they don’t sound like the work of one of the greatest geniuses in the history of music. Some of this was due to the people Miles was recording with. As Leo puts it, he went from being accompanied by the best bass player in the world to being accompanied by his coke dealer’s nephew. But the jazz world is more inclined to place the blame on Miles’ aesthetic choices instead. He always wanted to be in the musical present, not reliving the glories of the past, and it was especially important to him to be connected to young black audiences. In the 80s, that meant synths and drum machines, and music by Michael Jackson, Prince, and Cyndi Lauper. Towards the end of the decade, that also meant hip-hop. Miles’ last album was produced by Easy Mo Bee, who later went on to do Ready To Die with Biggie Smalls. Miles’ rap album isn’t a successful experiment, not least because he died before it was completed, but you can hear what he was trying to do. It’s taken the jazz world a few decades to catch up, but now that Robert Glasper and Thundercat are playing with Kendrick Lamar, it’s clear that Miles had the right idea.

So, all that is to say that while Miles’ recording of “Time After Time” isn’t particularly good, he at least recognized how gorgeous a song it is. Cassandra Wilson finished the work that he started, though with a very different aesthetic direction. I was moved by her version to do a mashup of it with Miles’ recording, Cyndi Lauper's original, a weird but wonderful cover by Willie Nelson of all people, and “The Score” by the Fugees, which references Cyndi in the lyrics. I’m pretty proud of it. You can download it here.